Season 2

1. Deathbowl '99

1999-01-31

1. Dolly Parton vs. Jennifer Lopez 2. Madonna vs. Michael Jackson 3. Mike Tyson vs. Evander Holyfield

2. The Battle of Boys With Toys

1999-02-04

1. Ice Cube vs. Ice-T 2. Robert DeNiro vs. Al Pacino 3. Backstreet Boys vs. Beastie Boys

3. Magic, Flashbacks and Pregnancies

1999-02-11

1. Calista Flockhart vs. Lucy Lawless 2. Boy George vs. Don Johnson 3. Penn & Teller vs. Siegfried & Roy

4. The Time Machine

1999-02-18

1. Jennifer Aniston vs. Courteney Cox vs. Lisa Kudrow 2. Sean Connery vs. Roger Moore 3. Gandhi vs. Genghis Khan

5. The Unknown Murderer

1999-02-25

1. Moses vs. Pharaoh 2. Larry King vs. Geraldo Rivera 3. Neve Campbell vs. Sarah Michelle Gellar

6. Celebrity Deathmatch Internacional

1999-03-04

1. Paul Hogan vs. Mel Gibson 2. Antonio Banderas vs. Cheech Marin 3. Fabio vs. Bono vs. Yoko Ono

7. The End of the Real World

1999-03-11

1. Kate Moss vs. Claudia Schiffer vs. Tyra Banks 2. William Shakespeare vs. Busta Rhymes 3. The Real World's: Puck vs. Jon vs. Tami vs. Jacinda

8. Celebrity Deathmatch - The Motion Picture

1999-04-22

It features fights that are about the elements of movies. The fights are Martin Scorsese vs. Oliver Stone in Fight 1, Fight 2 is Groucho Marx vs. John Wayne, and the Main Event is Cameron Diaz vs. Meryl Streep.

9. Cable Day

1999-05-06

1. Emeril Lagasse vs. The Two Fat Ladies 2. Matt Pinfield vs. Jesse Camp 3. Alex Trebek vs. Pat Sajak

10. 4th of July Celebration

1999-07-01

1. Bill Clinton vs. Kenneth Starr 2. James Van Der Beek vs. Saddam Hussein 3. Abe Lincoln vs. George Washington

11. Family Night I

1999-07-08

1. Charlie Sheen vs. Emilio Estevez 2. Eric & Julia Roberts vs. Donny & Marie Osmond 3. Bob & Jakob Dylan vs. Jerry & Ben Stiller

12. Censoring Problems

1999-07-15

1. Tommy Lee vs. Ron Jeremy 2. Alanis Morissette vs. Jewel 3. The Three Stooges vs. The Three Tenors

13. Salute to Laughter

1999-07-22

It's comedian time! 1. Dennis Miller vs. Carrot Top 2. Rodney Dangerfield vs. Don Rickles Main Event: Billy Crystal vs. Robin Williams vs. Whoopi Goldberg

14. The Laser Pointer

1999-07-29

1. Elton John vs. Ozzy Osbourne 2. Martha Stewart vs. Sandra Bernhard Main Event: Tom Hanks vs. Sean Penn

15. Robot Nicky

1999-08-05

1. Ricky Schroder vs. Gary Coleman 2. Lauryn Hill vs. Shania Twain 3. Hugh Grant vs. All-comers [ Clint Eastwood, Harvey Keitel, & Andy Dick ]

16. The Prophecy

1999-10-07

1. Dennis Franz vs. Sammo Hung 2. Steven Wright vs. Chris Tucker 3. Gwyneth Paltrow vs. Winona Ryder

17. In The Memory Of Stacy Cornbred

1999-10-14

1. Cher vs. Bette Midler 2. Benito Mussolini vs. Roberto Benigni 3. John Travolta vs. Nicolas Cage

18. From The Streets Of New York

1999-10-21

In this episode, the deathmatch cast interviews people in New York, about which fights they want to see.

19. Halloween Episode I

1999-10-28

1. Frankenstein's Monster vs. The Wolfman 2. Captain Doody vs. The Undertaker 3. 'N Sync vs. Kiss

20. High Tech Fighting

1999-11-04

1. Richard Simmons vs. Billy Blanks 2. Don King vs. Donald Trump 3. Brad Pitt vs. Keanu Reeves

21. Fandemonium II

1999-11-11

1. Ben Affleck vs. Matt Damon 2. Ozzy Osbourne vs. Rob Zombie 3. Marilyn Manson vs. Ricky Martin